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What happened? That's the question you end up asking yourself when surveying Adam Sandler's mega-successful and comedically questionable career. When the fresh-faced comedian emerged in the early '90s with Saturday Night Live bits like Canteen Boy, "Lunch Lady Land," and Opera Man, he was the silliest, most childlike star of the show's notorious bad-boy crew. We were all so innocent back then.

Along the way, something changed. Though he remains a big star, the 49-year-old comedian is tolerated by critics, mocked by his peers, and often slammed by the same fans who championed his early work. With the arrival of his latest Netflix comedy, The Meyerowitz Stories (New and Selected), we're taking stock of the Sand-Man's career (minus cameos in movies like Coneheads, Dirty Work, and Shakes the Clown) to track how baby voices, vacation destinations, and Rob Schneider cameos built a blockbuster career.

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38. Grown Ups 2 (2013)

Things that happen in Grown Ups 2: a deer pees on Sandler and Salma Hayek; Jon Lovitz leads the female cast members in a workout where the only exercise is chest shaking; bodybuilder Kris Murrell plays a character named "Beefcake Kitty," who romances David Spade, which is supposed to be icky because Beefcake is transgender; Shaquille O'Neal squeals and makes clown faces; Kevin James "burp snarts" (that's a burp-sneeze-fart combo, if you weren't familiar). Grown Ups 2 is a monumental step backwards for society at large. Never see it, but also never let Adam Sandler forget that he made it. -- Matt Patches

37. Jack and Jill (2011)

The only reason Adam Sandler's sub-sitcom twin movie isn't stewing at the bottom of this list is because it ends with Al Pacino singing and dancing in a Dunkin' Donuts ad about Dunkaccinos. Female Sandler breaking shit with a runaway Jet Ski sure didn't cut it. -- Matt Patches

36. Bedtime Stories (2008)

Sandler's bigger, zanier, messier take on Night at the Museum can be boiled down as such: [kooky fantastical event], [Adam Sandler gawking], [blockbuster set piece], [Adam Sandler screaming], repeat. The movie looks like it cost nine figures, and all that money buys one funny gag: Rob Schneider giving Sandler a Ferrari "for FREEEEEE." Now if the imagined rain of gumballs was more in the Roland Emmerich vein... -- Matt Patches

35. The Cobbler (2014)

In a movie that takes the phrase "walk a mile in someone's shoes" way too seriously, Sandler plays a cobbler who discovers a magical stitching machine in the basement of his Lower East Side shop that lets him commit crimes, harass women, and have a romantic dinner with his mother while... wearing someone else's shoes! If the nauseatingly whimsical, sub-Charlie Kaufman conceit wasn't bad enough, the movie piles on racist, sexist, and transphobic jokes that it mistakes for cutting social satire. If you thought this was another disposable product off the Happy Madison assembly line, think again: it was a passion project for director Tom McCarthy, who would follow it up with the Best Picture-winning Spotlight. Sandler wasn't as lucky -- his next movie was fucking Pixels. -- Dan Jackson

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34. Blended (2014)

What is it with Sandler and going on vacation? The true "auteur" of the comedian's films is his travel agent, who books the flights before a page of script is written. Blended reunites Sandler with his Wedding Singer co-star Drew Barrymore, but does not reunite him with jokes that land. It's a two-hour commercial for South Africa's Palace of the Lost City resort and a 5-year-old screaming "monster-ating” instead of “menstruating" kills any romantic spark. Sit Sandler and Barrymore in a nondescript room and they can make magic. Send them on a safari and the ostrich that Sandler insists on riding in a "hilarious" way pecks your eyes out. -- Matt Patches

33. Men, Women & Children (2014)

Juno and Up In the Air director Jason Reitman's Crash-for-the-Snapchat-generation ensemble drama is an abomination. Some highlights: Hank from Breaking Bad yells at his teen son for playing online role-playing games, Jennifer Garner tracks her daughter's cellphone usage like a CIA agent, and Emma Thompson narrates the whole thing in her best "T-Mobile commercial directed by Stanley Kubrick" voice. But, really, nothing beats the scene where you find out Adam Sandler was having sex with his wife on the morning of 9/11. Now, this is not a movie about 9/11 at all, but it's the type of film that's not above trying to plug a terrorist attack into its Mad Libs of alarmist buzzwords about "how we live now." There are Vines with more intellectual depth. -- Dan Jackson

32. Grown Ups (2010)

Next to Grown Ups 2, Sandler's first foray into family and friendship looks like The Big Chill. On its own, the movie's a brutal parade of sitcom setups and rejected Lockhorns jokes. The comedy supergroup of Kevin James, Chris Rock, David Spade, and Rob Schneider shouldn't have to try this hard. Maybe if Sandler, who casts himself as a dad who's just too successful and level-headed, tried at all. -- Matt Patches

31. TheRidiculous 6 (2015)

Like Seth MacFarlane with A Million Ways to Die in the West, Sandler chased the gaseous, fart-fueled flame of Blazing Saddles and ended up eating shit with his Western parody. There are a handful of funny jokes -- most of them involve Rob Schneider's diarrhea-prone donkey and Will Forte's eyepatch-sporting villain -- but Sandler, who handled co-writing duties on this one, doesn't exactly reveal himself to be a budding genre satirist. Instead of skewering cowboy conventions, it's mostly just another wacky, cameo-filled Happy Madison movie, only this time some of the characters wear 10-gallon hats, the period sets don't all resemble five-star resorts, and Vanilla Ice plays Mark Twain. It's the perfect movie to scroll past on Netflix when you're looking for something better. -- Dan Jackson

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30. Click (2006)

At some point in his career, Sandler became convinced he was a modern-day Jimmy Stewart. Spoiler alert: he is not. Nowhere is that more clear than this cloying, manipulative morality tale about a schlub who receives a magical remote control from a Bed Bath & Beyond employee played by Christopher Walken. Instead of having the decency to just be a forgettable comedy, the story becomes a bleak-as-hell drama about a workaholic who never has time for his family, neglects his wife, and ends up wasting his life. It begs for your tears and if you're an easy cry you'll end up bawling to a movie where Adam Sandler wears a fat suit. Stay strong. -- Dan Jackson

29. Eight Crazy Nights (2002)

It's perfectly acceptable to enjoy the "Chanukah Song," Sandler's pre-internet viral novelty hit. It's catchy, clever, and somehow remains the only Jewish holiday song with a great Rod Carew joke. But, man, what convinced a studio to make a whole mean-spirited animated film that exists mostly to remind people that, yes, the Chanukah song was good in the '90s? If you get excited by the idea of Sandler doing four grating character voices instead of just the usual one, this is your movie. Otherwise, skip this wannabe holiday classic. -- Dan Jackson

28. Sandy Wexler

For all the race-, gender-, and buffoon-baiting comedy in Sandler's modern repertoire, his most insufferable move is delivering a boring movie. Sandy Wexler, the third vehicle in Sandler's now-eight-picture Netflix deal, is a kind-hearted, underdog story that follows the worst manager in Hollywood as he helps angelic soul singer Courtney Clarke (Jennifer Hudson) take off. It's also entirely void of jokes. Every so often Nick Swardson's Evel Knievel wannabe crashes into food cart or a famous person shows up for a wacky cameo. Quincy Jones throws red wine in Sandy's face. Funny? Definitely lively. At one point, Sandy has a heart attack and his ventriloquist client (Kevin James) must Weekend at Bernie's his way through a pitch meeting. The "bits" are few and far between, and the interim manages to counter everything good (Hudson's voice) with something not so good (Sandler's wacky-dacky-doo voice). Sandy Wexler is stuck in limbo between Sandler's more committed turns, as if the goal was to produce the perfect Netflix background viewing. --Matt Patches

27. Going Overboard (1989)

Shot two years before Sandler joined Saturday Night Live and achieved real fame, Going Overboard is the no-budget, no-experience, no-worry version of Animal House. The jokes are sloppy. The plot is nonexistent (a comedian stows away on a cruise ship... then what???). Sandler constantly breaks the fourth wall like a horndog version of Ferris Bueller. Going Overboard is crude and relentless, what frat brothers might make on a boring, alcohol-fueled Sunday, and the camaraderie circles it back to mildly charming. -- Matt Patches

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26. The Do-Over (2016)

Adam Sandler must've loved the parts in The Fugitive about Devlin MacGregor. That's the only possible explanation for this high school reunion buddy comedy that morphs into an incomprehensible pharmaceutical thriller halfway through. The second of Sandler's increasingly bizarre projects for Netflix, the movie's sheer audacity is admirable -- it ends with David Spade discovering the cure for cancer, I think -- but the moments of absurdity are undercut by slack pacing, even-bad-for-a-Sandler-movie misogyny, and a disturbing amount of Corona product placement. You've gotta hand it to Sandler: even when he diverts from the formula, he still finds new ways to phone it in. -- Dan Jackson

25. Just Go With It (2011)

Sandler's throwback to golden-age rom-com farce is a total missed opportunity. Unlike co-star Jennifer Aniston, who understands the nuttiness required to fake being a guy's ex-wife so he can hook up with a blonde bombshell, then use the same guy to fake another relationship (switcheroo!), Sandler's lethargy can't juggle the antics. If you're going to repeatedly call your faux ex a drug-addicted floozy, muster up some playful energy! Whisking the audience to Hawaii is not a substitute. -- Matt Patches

24. Pixels (2015)

How limp is Sandler in this Ghostbusters-meets-video-games action movie? A CG Q*bert, who pees on the floor when he's scared, upstages the actor. Pixels works on some level; Harry Potter director Christopher Columbus keeps the action brisk and the retro game-inspired villains eye-popping. Sandler's the weak link, yet again playing a prodigy, a world-champion gamer who settles for a job at Geek Squad, and the hero. His shtick hits an immediate kill screen. -- Matt Patches

23. I Now Pronounce You Chuck And Larry (2007)

For a brief period in 2007, Adam Sandler was woke. The quietly conservative comedian has never exactly used his movies to champion specific causes -- unless keeping David Spade's career alive is a political act -- but this dumb comedy about two macho firefighters (Sandler and Kevin James) who apply for a marriage license to sidestep an insurance loophole also works as a piece of stealth social satire. The movie's gay-panic-joke-packed plea for tolerance isn't exactly revolutionary, but, hey, at least for one movie Sandler tried to use his power for something good, right? -- Dan Jackson

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22. Mixed Nuts (1994)

Sandler plays eighth fiddle in this stacked holiday comedy, though winds up with a few of the better scenes, including a heart-to-heart with Liev Schreiber's cross-dressing Chris, and a dinner-side serenade, performed with his usual affectation. On the scale of Nora Ephron movies, Mixed Nuts is a disaster. For Adam Sandler, it's in the middle of the pack. -- Matt Patches

21. Bulletproof (1996)

In some ways, Bulletproof is the platonic ideal of a forgettable '90s buddy comedy: elaborate and unfunny action sequences, sub-Shane Black-ian quips, an overwritten third act, and James Caan. For better and often for much, much worse, Sandler would never be this generic again. This is one of the few comedies in his filmography that he didn't co-write or produce, meaning it doesn't really feel like a "Sandler movie." Instead, it just feels like a regular old bad movie. -- Dan Jackson

20. Mr. Deeds (2002)

If you can get over the chutzpah it took for Sandler to cast himself as a modern-day Gary Cooper, this is actually one of his more digestible comedies. The "small-town yokel moves to the big city" narrative isn't really a good fit for Sandler's abrasive rageaholic schtick, but it was a smart choice to pair him with Winona Ryder as the love interest and stack the rest of the cast with fun performances from Peter Gallagher as the villain, Steve Buscemi as Crazy Eyes, and, in his first Sandler-verse appearance, John Turturro as a very, very sneaky butler. It's not Frank Capra, but it works if you want to watch 40 minutes of something on TBS before falling asleep. -- Dan Jackson

19. The Longest Yard (2005)

With none of the danger, off-color remarks, or racial commentary of Burt Reynolds' 1974 original, Adam Sandler's Longest Yard settles for the steady sophomoric shtick of his previous movies, with a smattering of prison football action. A five-yard pile-up of a movie, destined for lazy Saturday afternoon HBO viewing before cameras even rolled. -- Matt Patches

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18. Little Nicky (2000)

Sandler comedies tend to follow a pretty tight, well-tested formula that leaves little room for deviation, risk-taking, or elements that might scare away loyal fans. Maybe that's becasue he got nervous about messing with the blueprint after the commercial failure of Little Nicky, the most high-concept movie of the pre-Punch-Drunk Love era. Sandler doesn't play the normal schlub hero here, instead casting himself as Nicky, the favorite son of a devil (Harvey Keitel) who needs to find a new ruler of hell. Though the raspy-voiced Nicky character is grating, the silly world-building, ridiculous special effects, and light religious satire at least make this the weirdest of his non-terrible comedies. Points for originality! -- Dan Jackson

17. Reign Over Me (2007)

Adam Sandler's dramatic performances are a lot like Adam Sandler's comedic performances. In Reign Over Me, his character Charlie talks in a baby voice and jams to loud music, though instead of talking about "boobies," he's mourning the loss of his children, who died during 9/11. This sensitive, schmaltzy look at post-traumatic grief is some of Sandler's best work, no doubt, but his history of dopiness prevents us from fully buying into the comeback story. -- Matt Patches

16. Spanglish (2004)

Sandler can be effective in dramatic roles. It's just a shame those performances are typically in lackluster movies like Spanglish, director James L. Brooks' misconceived follow-up to his Oscar-winning hit As Good as It Gets. Sandler brings low-key charm, compassion, and an understated touch to his role as a chef struggling to keep his family together as his wife -- a combustible Téa Leoni -- battles her own demons. It's a movie that never really finds a rhythm and its awkward attempts to say something profound about the immigrant experience never quite connect, but that shouldn't stop you from checking it out for one of Sandler's best dramatic turns. -- Dan Jackson

15. Hotel Transylvania 2 (2015)

This inoffensive sequel to Sandler's sweet kids hit is more of the same: clever monster gags, zippy animation, and life lessons doled out with just enough deadpan humor for the adults to stay awake for the whole thing. This time Sandler's Dracula has anxiety about his half-vampire grandchild, particularly whether or not he's going to be raised as a monster or as a human. It's actually a potent metaphor for how different generations pass on cultural traditions and make compromises along the way, but luckily the movie doesn't attempt to reach for Pixar-style pathos. It wears its wisdom lightly, like a nice black cloak. -- Dan Jackson

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14. The Waterboy (1998)

"Now that's what I call high-quality H2O." With those words, a thousand GIFs were born, but before the internet turned Bobby Boucher into a meme, he was just a goofy movie character partially based on "The Excited Southerner" from Sandler's early comedy album. Boucher is one of Sandler's most iconic creations -- part innocent simpleton, part raging psychopath -- and this was his first massive hit, grossing over $185 million worldwide, but the film surrounding him isn't quite as memorable as the catchphrases. It's the type of movie that's more fun to quote than actually watch. Of course, that doesn't matter to superfans like Kanye West: they're too busy going Bobby Boucher to care. -- Dan Jackson

13. 50 First Dates (2004)

Reuniting Sandler with Drew Barrymore for a Memento-style memory-loss narrative isn't the worst idea in the world, and this Hawaii-set rom-com is always watchable. The two leads have real chemistry, the destination vacation setting doesn't feel like it's being rubbed in your face, and this was the movie where Sean Astin and Dan Aykroyd joined the Sandler-repertory company. Like Barrymore's amnesia-stricken character, you probably won't remember any of it the next day, but that's fine. Better to have mildly enjoyed and forgot, then to have never mildly enjoyed at all. -- Dan Jackson

12. Hotel Transylvania (2012)

As Sandler gets older and his image becomes more family-friendly, it only makes sense that he'd want to get in on the CGI-animated comedy boom of the last 10 years. Unlike the genuinely toxic Eight Crazy Nights, Hotel Transylvania is a surprisingly sweet, thoughtful movie about parenthood with a clever, gag-heavy script co-penned by Robert Smigel (Triumph the Insult Comic Dog) and dynamic, action-filled animation overseen by director Genndy Tartakovsky (Samurai Jack). Using a variation on his Opera Man voice, Sandler brings a light touch to this portrait of Dracula as an overprotective dad and the rest of the voice cast -- including Sandler regulars like Steve Buscemi, Kevin James, and David Spade -- makes the thing fly by. It makes you wonder why it took so long for Sandler, who has always had a gift for voices, to make one of these things. -- Dan Jackson

11. Big Daddy (1999)

While even early Sandler hits had sentimental parts, there was usually a healthy dose of irony to go with the romantic-comedy beats and faux-inspirational moments. But with Big Daddy things got downright mawkish. While the movie has some hilarious lines -- "We wasted the good surprise on you" still kills -- this oaf-meets-cute-kid tale is mostly notable for a lengthy Sheryl Crowe-scored montage, a big Mrs. Doubtfire-style courtroom finale, and the welps of "Scuba Steve!" This was the first time Adam Sandler figured out he could make bros cry. Sadly, he's mostly used that power for evil ever since. -- Dan Jackson

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10. Airheads (1994)

The mid-'90s: when Brendan Fraser was a bigger star than Adam Sandler and the movies were better for it. This grungy take on Dog Day Afternoon ranks among Sandler's best because it's a real movie, with stakes -- a rock band takes a radio station hostage! -- consequences, and a Cameron Crowe-esque musical backbone. Fraser, Sandler, and Steve Buscemi deliver as head-banging nincompoops, waxing poetic on heavy-metal icons ("Who'd win in a wrestling match, Lemmy or God? ... trick question -- Lemmy IS God") and flailing when they need to step up to be criminals. There's a reason Comedy Central played this nonstop in its heyday: Airheads is dopey bliss. -- Matt Patches

9. Anger Management (2003)

The biggest failing of Anger Management is that it's an OK movie that promises to be Sandler's greatest achievement. Pairing the furious comedian with the legendary Jack Nicholson at his most wily, the absurd story of one man's attempt to calm down is just another slapstick, screamy TV-episode-gone-big-screen, Meet the Parents without any of the undercurrent. But Jack Nicholson's in it! And Sandler really knows how to lose his shit. So we have a soft spot for this one. -- Matt Patches

8. Funny People (2009)

Funny People is easy to admire in the abstract: after the commercial success of The 40-Year-Old Virgin and Knocked Up writer-director Judd Apatow teamed up with his old friend the Sand-man for a slightly meta, James L. Brooks-ian examination of comedy, disease, and death. And, for many scenes, this movie feels like nothing else you've ever seen, and Sandler feels caustic, biting, and alive in ways that he's never been on screen before. It's hard to pinpoint exactly where the movie goes wrong in its 146 minutes -- maybe that insane running time is itself the fatal flaw -- but it's exciting to think that Sandler, a risk-averse comedian who seems to use his movies as vacation packages for his friends and family, decided to star in a movie this odd, messy, and personal. -- Dan Jackson

7. That's My Boy (2012)

If you grew up enjoying Sandler's incredibly filthy comedy albums, you've probably spent the last few decades asking yourself this question: where's the dirty stuff? Apparently he was saving it all for this underrated gross-out farce, which finds Sandler playing the obnoxious Boston deadbeat father of Andy Samberg's uptight social-climber. Freed from the constraints of the PG-13 rating -- and routinely pushing the edges of the R with jokes about statutory rape, incest, and, uh, jizzing on wedding dresses -- the movie lets Sandler be as disgusting and blue as you always knew he was capable of. It's not pretty but it's chasing something Sandler comedies have lacked for a while: actual laughs. -- Dan Jackson

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6. You Don't Mess with the Zohan (2008)

Unlike Will Ferrell, Ben Stiller, and other contemporaries, Sandler stays away from "high concepts." Most of his movies play like Everybody Loves Raymond episodes with $70 million budgets. Zohan is the polar opposite, an action comedy with a hyper-specific character -- an Israeli counter-terrorist becomes an NYC hairstylist! -- and absurd laws of physics. There are fits of physical comedy and hummus jokes galore. The movie was one big risk. Sandler seems aware -- he gives Zohan all he's got. -- Matt Patches

5. The Meyerowitz Stories (2017)

After releasing three of his original comedies in the last two years -- Ridiculous Six, The Do-Over, and Sandy Wexler -- Netflix finally cranked out a really good Adam Sandler movie. The Noah Baumbach-directed effort is a departure that still understands what's funny, charming, and potentially alienating about Sandler's persona. (He even gets to sing silly songs on the piano at one point.) Along with Dustin Hoffman, Ben Stiller, Emma Thompson, and the very sharp Elizabeth Marvel, Sandler plays a member of the Meyerowitz family, a uniquely miserable group of people united by their thinly veiled resentment towards one another. Splitting the difference between the caustic misanthropy of The Squid and the Whale and the freewheeling absurdity of his recent Greta Gerwig film, Mistress America, the movie finds both Baumbach and Sandler at the peak of their powers.

4. Happy Gilmore (1996)

Sandler has returned to the dude-friendly, cliche-filled sports movie well over the years, but this slobs vs. snobs comedy about a hockey player-turned-golf pro earns its gold jacket. It's got the funniest cameos (God bless Bob Barker), the most loveable sidekick (RIP Chubbs), the best villain (Christopher McDonald's sniveling Shooter McGavin), and even the product placement for Subway is funny ("Talk about a hole in one!"). Two decades of people incessantly quoting the movie out on the links still can't zap this thing of its long-drive-hitting, magical power. Even if you can't stand Sandler, it's worth a watch. But do whatever you like. What would I know? I'm just a doctor. -- Dan Jackson

3. The Wedding Singer (1998)

Sound the alarms: Adam Sandler has actual chemistry in a movie! The Wedding Singer takes advantage of Sandler's musical talents and inherent schlubiness for a storybook romance. Drew Barrymore is like a lost John Hughes lead, sweetening the frat-house comedy. '80s nostalgia never looked, or sounded, so good. -- Matt Patches

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2. Billy Madison (1995)

No stupid '90s comedy benefits more from the Saturday afternoon Zapruder-film rewatching experience than Billy Madison, the rich-idiot-goes-back-to-school movie that made Sandler a god to 12-year-olds across the country and set him on the path to world-conquering stardom. While the classic baby-talk Sandler bits, like shampoo vs. conditioner, still work, it's the small details, like Bradley Whitford complaining about Triscuits crackers, Chris Farley making out with a penguin in a field, Steve Buscemi quietly crossing Billy's name off his kill list, and the off-hand way Norm Macdonald says "October" that really make this an absurd slacker masterpiece. -- Dan Jackson

1. Punch-Drunk Love (2002)

Paul Thomas Anderson's furious romantic comedy is the Pluto to Sandler's filmographic solar system. You can't help but doubt it -- does it even count as an Adam Sandler movie? And yet the pieces are there: the comedian plays Barry, a novelty plunger salesmen who battles his malicious sisters, a shadowy phone-sex extortionist, and the crippling effects of depression, all while falling in love with the women of his dreams. With brighter lighting and a top-40 soundtrack, it would follow in the tracks of Happy Gilmore and Big Daddy. In Anderson's hands, it's a melancholic character study that strangles Sandler's persona with his own vocal chords. The colors are dreamlike. The anger is palpable. Sandler bursts from the seams of his own fame. It's everything we want from a funnyman-gone-serious, caustically sweet and mentally unstable, an alternative mode that Sandler's hero complex would never revert to again. -- Matt Patches

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